Synthesis of 2-Aryl-4-arylazo-2-thiazolin-5-ones and their reaction with aromatic amines

1976 ◽  
Vol 29 (7) ◽  
pp. 1627 ◽  
Author(s):  
AM Khalil ◽  
IIA El-Gawad ◽  
HM Hassan
Keyword(s):  
Acetic Acid ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Diazonium Salt ◽  
Coupling Reaction ◽  
Catalytic Amount ◽  
Heterocyclic Ring ◽  
Primary Aromatic Amines

2-Aryl-4-arylazo-2-thiazolin-5-ones are prepared by a coupling reaction between thioaroylglycine and the appropriate diazonium salt. Their heterocyclic ring is readily opened by the action of primary aromatic amines in acetic acid containing a catalytic amount of sodium acetate with the formation of 1,5,Nx-triaryl-1H-l,2,4-triazole-3-carboxamides.

The action of arylamines on some substituted 2-Thiazolin-5-ones

1974 ◽  
Vol 27 (9) ◽  
pp. 2035 ◽  
Author(s):  
AM Khalil ◽  
El-Gawad II Abd ◽  
M Hammouda
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Heterocyclic Ring ◽  
Reaction Conditions ◽  
Primary Aromatic Amines

The heterocyclic ring in 2-aryl-4-arylmethylene- and 4-arylmethylene-2-benzylthio-2-thiazolin-5-ones is readily opened by the action of primary aromatic amines in acetic acid containing a catalyticamount of sodium acetate with the formation of 1,2-diaryl-4-arylmethylene-2-imidazolin-5-ones and of 3-aryl-5-arylmethylene-2-thiohydantoins respectively. 4-Benzylidene-1-(p-chloropheny1)-2-phenyl-2-imidazolin-5-one was also obtained by the cyclization of the anilide of α-(p-chlorothiobenzamido)-β-phenylacrylic acid under the same reaction conditions. A possible reaction mechanism is postulated.

Cyclisation of 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoins

1981 ◽  
Vol 36 (4) ◽  
pp. 501-504 ◽  
Author(s):  
A. F. A. Shalaby ◽  
M. A. Abdel Aziz ◽  
S. S. M. Boghdadi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Mannich Bases ◽  
Anhydrous Sodium Acetate ◽  
Primary Aromatic Amines ◽  
Hydantoin Derivatives

Abstract 1-Phenyl-4-carboxymethylmercapto-5-arylazo-hydantoin derivatives (3a-f) were cyclised with acetic anhydride to give the bicyclic products (4a-f). Compounds 4 a, b condensed with aromatic aldehydes in acetic acid and in presence of anhydrous sodium acetate yielding the corresponding arylidene derivatives (5a-c). Compounds 4a, b also couple with aryldiazonium salts to give the expected coloured arylazo compounds (6a-j). 4 a, b reacted with formaldehyde and primary aromatic amines in ethanol to give the corresponding Mannich bases (7a-f).

Reaction of 2-Aryl-4-arylmethylene-2-oxazolin-5-ones with amines

1973 ◽  
Vol 26 (4) ◽  
pp. 827 ◽  
Author(s):  
AM Islam ◽  
AM Khalil ◽  
El-Gawad II Abd
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Reaction Conditions ◽  
Primary Aromatic Amines

1,2-Diaryl-4-arylmethylene-2-imidazolin-5-ones were prepared by the interaction of primary aromatic amines with 2-aryl-4-arylmethylene-2- oxazolin-5-ones in the presence of acetic acid and sodium acetate. The same imidazolones were also obtained by the cyclization of the arylamides of α-arylamido-β-arylacrylic acids under the same reaction conditions. A possible reaction mechanism was postulated.

Reaction of 2-(m-Tolyl)-4-arylmethylene-2-oxarolin-5-ones with amines

1973 ◽  
Vol 26 (8) ◽  
pp. 1701 ◽  
Author(s):  
AM Islam ◽  
AM Khalil ◽  
MS El-Houseni
Keyword(s):  
Acetic Acid ◽  
Reaction Mechanism ◽  
Aromatic Amines ◽  
Sodium Acetate ◽  
Direct Interaction ◽  
Reaction Conditions ◽  
Primary Aromatic Amines ◽  
Facile Route

A facile route for the preparation of 1,2-diaryl-4-arylmethylene-2-imidazolin-5-ones was established by the direct interaction of primary aromatic amines with 2-(m-tolyl)-4-arylmethylene-2-oxazolin-5-ones in acetic acid containing catalytic amounts of sodium acetate. The same imidazolones were also obtained by cyclization of the aryl- carboxamides of α-arylcarboxamido-β-arylacrylic acids under the same reaction conditions. A possible reaction mechanism was discussed.

The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1623-1632 ◽  
Author(s):  
Elina Marinho ◽  
M. Proença
Keyword(s):  
Acetic Acid ◽  
Trifluoroacetic Acid ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Ethyl Chloroformate ◽  
Convenient Synthesis ◽  
Primary Aromatic Amines

2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

scholarly journals New developments in dimethyl carbonate chemistry

2001 ◽  
Vol 73 (7) ◽  
pp. 1117-1124 ◽  
Author(s):  
Pietro Tundo
Keyword(s):  
Aromatic Amines ◽  
Dimethyl Carbonate ◽  
Catalytic Amount ◽  
Inorganic Salts ◽  
Cyclic Ketones ◽  
Carbonate Chemistry ◽  
Methyl Halides ◽  
New Developments ◽  
Primary Aromatic Amines ◽  
By Products

Dimethylcarbonate (DMC) is a valuable methylating reagent which can replace methyl halides and dimethylsulfate in the methylation of a variety of nucleophiles. It couples tunable reactivity and unprecedented selectivity toward mono-C- and mono-N-methylation in the reactions of acidic CH2 and primary aromatic amines, respectively. In addition, it is a prototype example of a green reagent, since it is nontoxic, made by a clean process, and biodegradable, and it reacts in the presence of a catalytic amount of base thereby avoiding the formation of undesirable inorganic salts as by-products. Other remarkable reactions are those where DMC behaves as an oxidant: cyclic ketones are transformed into a,w-dimethyl esters with a reaction of atom efficiency of 1.0.

scholarly journals REACTION OF 2-HETARYL-2-(DIHYDROFURAN-2(3H)-ILIDEN)ACETONITRILES WITH AROMATIC AMINES

2020 ◽  
pp. 47-51
Author(s):  
R. Shemehen ◽  
O. Khilya ◽  
Yu. Volovenko
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Catalytic Amount ◽  
Building Blocks ◽  
Heterocyclic Ring ◽  
Ring Closure ◽  
Reaction Conditions ◽  
Ring Opening Reaction ◽  
Ring Transformations ◽  
High Yields

This article reports on the reaction of 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles with aromatic amines as N-nucleophiles. 2-Hetaryl-2-(furanyl-2-ylidene)acetonitriles represent versatile building blocks in syntheses of ω-(N-aryl)alkyl substituted heterocycles due to the presence of 1,3-bielectrophilic acrylonitrile fragment functionalized with unsaturated heterocyclic ring and nucleophilic azaheterocyclic moiety. The carbonyl group masked within the N-arylpyrrolidinylidene fragment which undergoes a ring opening through the reaction with nucleophiles. So, a method for the synthesis of 2-hetaryl-6-hydroxy-3-(arylamino)hex-2-enenitriles and 2-hetaryl-2-(N-arylpyrrolidin-2-ylidene)acetonitriles has been developed by us. The proposed scheme is based on the available reagents using. As a result of Michael addition, the aromatic amines to 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles followed by ring transformations has formed two types of products, depending on the reaction conditions. The reaction of substituted furanylylideneacetonitriles with aromatic amines proceeds in good to high yields affording the corresponding 3-(arylamino)hex-2-enenitriles and 2-(N-arylpyrrolidin-2-ylidene)acetonitriles derivatives. The stereochemistry of the ring-opening reaction follows the rules of a classical SN2 mechanism. The resulting linear products can be cyclized to 2-hetaryl-2-(furanyl-2-ylidene)acetonitriles in high yields by treatment with the catalytic amount of acid or the equimolar amount of aromatic amines. Under these conditions 2-hetaryl-6-hydroxy-3-(arylamino)hex-2-enenitriles arising from reaction gives the ring closure. Since both ring-opening and cyclisation occur with fixed stereochemistry the reaction appears a valuable modification to the preparation of acetonitriles derivatives.

scholarly journals Synthesis, Characterization and Biological Evaluation of Some Pyrrole Derivatives as Potential Antimicrobial Agents

2021 ◽  
pp. 757-770
Author(s):  
Safiya R. Shaikh ◽  
Hanmant S. Mali ◽  
Shubhangi S. Thorat ◽  
Vishwajit D. Dhaygude ◽  
Muskan M. Bhaldarakar ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Acetic Acid ◽  
Side Effects ◽  
1H Nmr ◽  
Aromatic Amines ◽  
Antimicrobial Agents ◽  
Biological Evaluation ◽  
Efficient Synthesis ◽  
Pyrrole Derivatives ◽  
Primary Aromatic Amines

Novel series of pyrrole derivatives were synthesized with an approach to develop more potent and less side effects having antimicrobial activity. An efficient synthesis of different novel 2-methyl-7(4-nitrophenyl)-5,6-diphenyl-3,7-dihydro-4H-pyrrolo-[2,3-d]pyridine-4-one derivatives by the Paal-knorr Condensation. Benzoin with primary aromatic amines refluxing in ethanol resulted the formation of α-aminoketone intermediates, which were condensed, without isolation, with malononitrile to yield the various 2-amino-4,5-diphenyl-1-substituted-1H-pyrrole-3-carbonitriles (Ia-e). Pyrrole (Ia-e) further reacted with acid such as acetic acid to yield compound (IIa-e). The synthesized compounds were confirmed through spectral characterization using IR, Mass and 1H NMR. Result indicated that these compounds showed promising antimicrobial activity by comparing to standard drugs.

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